(R)-3-(4-(8-isopropyl-5-oxo-4-propyl-4,5,7,8-tetrahydro-1H-imidazo[1,2-g]purin-2-yl)bicyclo[2.2.2]octan-1-yl)propanoic acid

ID: ALA216200

PubChem CID: 135428653

Max Phase: Preclinical

Molecular Formula: C24H35N5O3

Molecular Weight: 441.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1C(=O)N2C[C@@H](C(C)C)N=C2c2[nH]c(C34CCC(CCC(=O)O)(CC3)CC4)nc21

Standard InChI:  InChI=1S/C24H35N5O3/c1-4-13-28-20-18(19-25-16(15(2)3)14-29(19)22(28)32)26-21(27-20)24-10-7-23(8-11-24,9-12-24)6-5-17(30)31/h15-16H,4-14H2,1-3H3,(H,26,27)(H,30,31)/t16-,23?,24?/m0/s1

Standard InChI Key:  SYGGDNIWKSBCDC-JEACLXLTSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   -1.6125   -1.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6627   -0.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205   -0.2651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973    1.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9498    1.8334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8223   -3.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1482   -4.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8066   -5.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6120    1.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4602    0.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9082    1.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3211    2.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2810    3.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8329    3.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4966    2.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2244    1.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2125   -2.9168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7628    2.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7814    1.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2455    2.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6018    3.2462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0600    1.2190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3414   -0.5743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5683    0.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5402    1.8334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9539    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8214   -0.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2446    1.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2894    1.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2338    3.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  4  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  3  7  1  0
  6  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 11 16  1  0
 15 16  1  0
 11 17  1  0
 14 18  1  0
 17 18  1  0
  1 19  2  0
 14 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
  1 25  1  0
  3 26  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 25 29  1  0
 28 29  1  0
 28 30  1  1
 30 31  1  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA216200

   ---

2. Alternative Forms:

   

   ALA216200

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 441.58

Molecular Weight (Monoisotopic): 441.2740

AlogP: 4.30

#Rotatable Bonds: 7

Polar Surface Area: 101.89

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.87

CX Basic pKa: 5.09

CX LogP: 2.64

CX LogD: 0.81

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.66

Np Likeness Score: 0.09

References

1. Vu CB, Kiesman WF, Conlon PR, Lin KC, Tam M, Petter RC, Smits G, Lutterodt F, Jin X, Chen L, Zhang J..  (2006)  Tricyclic imidazoline derivatives as potent and selective adenosine A1 receptor antagonists.,  49  (24): [PMID:17125265] [10.1021/jm060539t]

Source

Source(1):

• Scientific Literature